my mom has owed me nearly $300 for almost a month now. she's usually good about paying back money she owes, but this time things have caught her off guard, so it's taking her longer than usual. it does annoy me a bit having to remind her, but i know she'll eventually pay me back. the first few times i had to remind her it was a bit uncomfortable because she'd get annoyed, but over time it has gotten better. it helps that she was eventually upfront and told me it may take her a while to pay me back. i told her that as long as i know that she'll eventually pay me back, she can take her time and pay off other things that really, really need to be taken care of first.

asking for money back is incredibly uncomfortable for me. i feel that it depends on the relationship you have with the person you loaned the money to, but you can always just say "hey, i loaned you money a while back, any idea when i'll be getting it back?" if the person sincerely says "i'm struggling right now, give me a few days or weeks" i'd say that's fine, but if the person gets upset and doesn't even bother to give you a time frame, you might as well consider that money lost.